Organopolysiloxanes are excellent in heat resistance, weatherability, releasability, water repellency, and physiological inertness and are used in various fields. Modified organopolysiloxanes obtained by modifying hydrophobic organopolysiloxanes with a hydrophilic compound to thereby impart surface-active properties thereto are also in general extensive use. Among such modified organopolysiloxanes are polyoxyalkylene-modified organopolysiloxanes obtained by organopolysiloxane modification methods such as, for example, a modification reaction between a polyoxyalkylene having a hydroxyl group at an end and an organopolysiloxane having one or more alkoxy groups, a hydrosilylation modification reaction between a polyoxyalkylene having a double bond, e.g., an allyl group, at an end and a hydrogenorganopolysiloxane, and a modification reaction between a polyoxyalkylene having an epoxy group at an end and an organopolysiloxane containing one or more amino groups. Of these, the hydrosilylation modification reaction is in frequent use. With respect to nonionic modified organopolysiloxanes obtained by the hydrosilylation modification reaction, polyoxyethylene groups are used as a highly hydrophilic modifying group among the polyoxyalkylene groups in more frequent use. However, many modified organopolysiloxane compounds having alcoholic hydroxyl groups, which have even higher hydrophilicity than the oxyethylene group, as a modifying group have been proposed so far. Examples thereof include a modified organopolysiloxane having a glycerol residue, a modified organopolysiloxane having a polyglycerol residue, and a modified organopolysiloxane having a sugar residue. With respect to the modified organopolysiloxane compound having a sugar radical, among those modified organopolysiloxanes, many compounds and processes for producing these have been proposed as shown below.    1) A process for producing a compound which comprises reacting sorbitan with allyl glycidyl ether in the presence of an alkali catalyst to obtain a precursor and subjecting the precursor to hydrosilylation with a hydrogenorganopolysiloxane to obtain the target compound. (e.g., patent document 1)    2) A process for producing a compound which comprises mixing an amino-modified silicone with a sugar lactone and heating the mixture to obtain the target compound through amidation. (e.g., patent document 2)    3) A compound obtained by subjecting a glucoside having an alkenyl group, e.g., allylglucoside, and a hydrogenorganopolysiloxane to hydrosilylation; and a process for producing the compound. (e.g., patent document 3)    4) A compound obtained by subjecting glucose and allyl glycol to dehydrating condensation using a p-toluenesulfonic acid catalyst to obtain a precursor and modifying the precursor with a hydrogenorganopolysiloxane; a process for producing the compound; and a process for production in which an allyl-glycol-modified organopolysiloxane and glucose are subjected to dehydrating condensation. (e.g., patent document 4)    5) A compound obtained by reacting an acetylated sugar with allyl alcohol to obtain a precursor, subjecting the precursor and a hydrogenorganopolysiloxane to hydrosilylation, and decomposing the acetyl groups with sodium methoxide; and a compound obtained by reacting an acetylated sugar with thiourea to obtain a precursor, reacting the precursor with an organopolysiloxane having halogen radicals, and decomposing the acetyl groups with sodium methoxide. (e.g., patent document 5)    6) A process for producing a compound which comprises subjecting a sugar and an intermediate-coupling-chain precursor having a double bond to dehydrating condensation using a p-toluenesulfonic acid catalyst and modifying the condensate with a hydrogenorganopolysiloxane. (e.g., patent document 6)    7) A compound obtained by reacting an acetylated sugar with allyl alcohol to obtain a precursor, subjecting the precursor to an addition reaction with a thiocarboxylic acid or thiol compound to obtain a metal thiolate, and then subjecting the thiolate to a condensation reaction with an organopolysiloxane having halogen radicals. (e.g., patent document 7).
Of those prior-art techniques, 1) and 6) have a possibility that the modification reaction of the precursor having a sugar residue with the reactive organopolysiloxane might result in gelation or resinification because the precursor is a compound which has, per molecule, two or more functional groups reactive with the organopolysiloxane. With respect to 2), since a compound having amino groups is used, there are a problem concerning the odor attributable to the compound and the possibility of discoloration. With respect to 3), 4), 5), and 7), there is a possibility that use of the product compounds might be limited because the glucoside residues as a modifying group have a structure unstable to acids and heat. None of the modified organopolysiloxane compounds which have been found so far, including the modified organopolysiloxane having a glycerol residue described above and the modified organopolysiloxane having a polyglycerol residue described above, is one which can have hydrophilicity effectively imparted thereto with a raw material incorporated even in a smaller amount. Furthermore, no process has also been found in which precursor formation can be controlled so that only one functional group per molecule can be introduced into the precursor and by which a modified organopolysiloxane having sugar residues can be efficiently produced.    Patent Document 1: JP-A-57-209295    Patent Document 2: JP-A-62-68820    Patent Document 3: JP-A-5-186596    Patent Document 4: JP-A-6-316590    Patent Document 5: JP-A-11-92490    Patent Document 6: JP-A-2002-119840    Patent Document 7: JP-A-2003-146991